Ontology highlight
ABSTRACT:
SUBMITTER: Liu Z
PROVIDER: S-EPMC3204185 | biostudies-literature | 2011 Nov
REPOSITORIES: biostudies-literature
The Journal of organic chemistry 20111004 21
A nonisosteric α-C-glycoside analogue of KRN7000 (α-1C-GalCer, 1) was reported to induce a selective type of cytokine release in human invariant natural killer cells in vitro. We report here a very concise synthetic route to 1 and its analogue 1'. The key steps include olefin cross-metathesis, Sharpless asymmetric epoxidation, and epoxide opening by NaN(3)/NH(4)Cl. Inversion of configuration at the amide-bearing carbon in the phytosphingosine backbone constructed by epoxide opening in our previo ...[more]